Tails Explores His Feelings (or something)
by RetroSpaghetti
Summary: I don't really know what to put here, I'm just writing this for fun. Right now though Tails is exploring his gender, or something like that. May include SonTails in future chapters, depending on which direction I want to take it. I'll put a warning in the chapter name though, to save those who do not like it.
1. Chapter 1

**It's been a very long time since I've written a fanfic, and this is a new topic for me. So it may not be of the utmost quality, I apologise in advance.**

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'Today was pretty average, nothing much out of the ordinary happened. I think I may have accidentally let my secret slip to Cream, she may have suspicions but it should be nothing more than that...'

Suddenly, there was a knock at the door and Tails jumped up, frantically trying to find a place to hide the diary. Before he could, Amy opened the door to find Tails standing there with one hand suspiciously behind his back.  
"H-hey Amy!" Tails stuttered, sitting back down on his bed and yet again looking for a place to store the diary, eventually settling for just putting it under the duvet.  
"Hi, Tails! You coming down yet? We're all playing video games!" Amy yelled as she always does, but slowly quietened her voice upon noticing Tails hiding something.  
Tails nodded slightly, stood up and left the room with Amy following shortly behind. The loud cries of Sonic and the rest of friends could be heard from the top of the stairs, though it's probably nothing.  
"I'm just going to go to the loo, I'll be down in a moment." Amy continued, making her way to the bathroom. Tails decided to give Amy some privacy and walked downstairs to join the others. The moment Tails was out of earshot, Amy rushed out of the bathroom and back into Tails' room, quickly rummaged under the covers and found the diary. She grinned slightly but decided not to read it now to avoid suspicion, so she left Tails' room and slipped it into her bag on the staircase.  
"Amy come over here! Knuckles is destroying this game!" Sonic shouted from the other room, waving a hand around the doorway. Amy rushed back in to join them.

Hours later, Amy picked up her bag and left with the others. All parting their separate ways.  
"Hey Cream, come here a sec," Amy put her hand on Creams shoulder and pulled her aside, "I've got something to show you, come with me!" Not giving Cream a chance to respond, Amy dragged her back to her house.  
Sitting in the living room of her house, Amy pulls out the diary and shows it to Cream, who lets out a little gasp at the sight.  
"Amy! We can't read this, can we?" Cream rested the diary down on her lap, giving Amy a look of confusion mixed with curiosity.  
"Well, why not? It's not like he'll ever find out." Amy snatched the book back from Cream and flicked to a random page, skim reading at first, but soon moving her head closer and reading very carefully.  
"What is it? You look shocked," Cream said, still looking at Amy, and then at the diary.  
"You have to read this," Amy whispered, slowly handing the book to Cream. Cream looks at the book, she hadn't yet decided whether it's okay to read or not, but soon talked herself into it.  
She too, read it slowly and was shocked at what she'd found. She looked up at Amy, unsure of what to do or say.  
"We should do something about this," Amy started, trying to think of a good way to handle the situation, "Maybe I should approach him about it."  
"I don't think that's a good idea, if anyone should talk to him it should be me. He's more comfortable around me." Cream stated, closing the book and putting it on the table.  
"That sounds like a better idea," Amy continued, "Shall I put the kettle on?"  
"I think I'm going to head home, it's getting late" Cream too stood up, and made her way to the door, "Just make sure to return the diary, okay?"  
"Don't worry, I will. See you tomorrow!" Amy shouted, waving goodbye to Cream as she stepped out the door.

The next day, Tails was searching his bedroom once again, not for a hiding place but for the diary itself.  
"Oh god, oh god where is it?" Tails mumbled to himself, not quite remembering where he had put it the day before. Though he calmed down upon thinking to himself "If I can't find it, surely nobody else can."  
He sat down on his bed, thinking about what to do now. He'd almost thought of something but his phone suddenly made a noise, it was a text message from Cream.  
"Hey, can you come over? I wanna hang out!"  
Tails was delighted, he'd always enjoyed spending time with Cream. So did not hesitate to respond.  
"Yeah I'm free, I'll be there in a minute!" Tails responded, quickly rushing to gather his things and make his way out.

Tails knocked on the door of Creams house, but there was no response. He waited a little bit and knocked again, this time there was a shout from inside.  
"It's unlocked, come in. I'm upstairs if you wanted to come up!" Cream rarely ever shouted, Tails was happy to hear her this excited. He walked in and made his way up to the stairs. He'd rarely ever come up there, so he knocked on her bedroom door just to make sure. Cream let out a little "Come in!" Tails opened the door to see Cream, wrapped in a pink duvet, sitting on her bed. Her usual clothes were laid out in front of her, Tails was taken aback slightly.  
"Uh Cream, are you..."  
"No of course not, I'm wearing pyjamas." Cream said quietly, she was blushing slightly at the thought.  
"What is this about?" Tails tore his eyes away from Cream and down to her dress, it looked pretty, he thought.  
"You seem pretty fixated on the dress there, huh?" Cream looked at Tails once again, his seemed shocked at this remark.  
"U-uh, n-no!" Tails blurted, taking a few steps back.  
"Did you want to try it on? I think it'd look real cute on you!" Cream was now holding up the dress to see what it'd look like on Tails. He let out a little sigh and walked towards Cream, feeling the material of the dress. He put the dress down, suddenly realising what had happened.  
"You've read my diary, haven't you?" Tails looked back at Cream with an angry expression.  
"That doesn't matter now, all that matters now is that I want to help you!" Cream looked deep into Tails' eyes, watching the anger fade.  
"Do you really think it'd look good on me?" Tails was blushing now, holding the dress up against himself.  
"Of course! You'd look adorable! Now go put it on!" Cream gestured for Tails to go and change in her closet, which he did in an instant.  
Tails stepped inside the closet and became overwhelmed at the number of pretty dresses and skirts he'd found himself surrounded by. Clearing his mind, he decided to just focus on this one dress, as too much too fast would be too stressful.  
The dress was on now on Tails, he looked around for a mirror but couldn't find one. He reached for the door handle of the closet but moved away slowly, "I can't do this" he thought "this is too much."  
Suddenly, Cream shouted from outside "Come on Tails, it'll be fine!"  
This gave him some courage, he put his hand on the doorknob once again and turned it slowly.

Tails stepped out of the closet, wearing Creams goto dress, only to find not one person sitting on the bed, but two. Tails fell to his knees, it really was too much for him to handle. He looked up at Cream, then at Amy and finally at the ground. He didn't know what to do, for a while there was just silence, until Cream decided to speak.  
"Tails..." She started "You look fantastic!" This made Tails look up, Cream was overjoyed and by the looks of it Amy was too. He stood up slowly and went to sit down between the two. Tears were welling up in his eyes, this kind of thing had always made him emotional though he wasn't sure why. He pushed back the tears and looked at Cream.  
"You really think so...?" Tails cried, no longer able to hold back the tears he turned to Amy. She nodded, her hands obscuring her mouth slightly. Despite the tears, Tails was happy.  
"Of course! You look really pretty!" Amy stood up quickly and turned to Tails, she put her hand in his and pulled him up in for a hug. Tails was openly weeping now and Amy hugged him tighter.  
"It's okay, we're here for you Tails," Amy said, rubbing his head "We're soo proud of you!"

A little time passed and they were all sitting on the bed once again, Tails had stopped crying now.  
"I'm sorry guys, I don't know what's wrong with me." Tails apologised, twiddling his thumbs.  
"There's nothing wrong with you Tails, I'm glad we were able to do this. Even if we had to read your diary." Amy giggled.  
"I'm still mad about that!" Tails huffed, though he wasn't really that mad. They'd helped him explore himself after all.  
"We're really sorry about that." Cream croaked, looking over at Tails "If you ever want to do anything like this again, just text me. Okay?"  
This made Tails look up at Cream, he could feel the tears coming back again, but he was strong this time.  
"Yeah! Maybe we can get you in a skirt next time!" Amy threatened, jabbing Tails with her elbow, making Tails let out a little laugh.  
"As much as I would want to, I'm not sure I'm quite ready for that amount of stress just yet." Tails stood up once more, "Thank you guys soo much, this has been eating me up inside for too long."  
"It's no problem, we love this kind of stuff, and we'd be happy to help any time!" Cream was incredibly enthusiastic about the whole situation, more so than Amy.  
"Well anyway, should I take this off now? I've got to get going." Tails asked, holding up the ends of the dress with his hands.  
"Nah, you can take that one with you!" Cream grinned, standing up as well.  
"I couldn't, this is your..." Tails started, but was quickly cut off.  
"Just take it!" Cream implored.  
"Okay, okay!" Tails was overjoyed, he now had his very own dress!  
Soon, they were all parting ways, Amy walking back to her house and Tails walking back to his, dress in hand.


	2. Chapter 2

"So is it a sexual thing?" Amy asked, giving Tails a strange look.  
"AMY!" Cream snapped, gently punching Amy in the arm, "You can't just ask him stuff like that!"  
"Okay okay!" Amy laid back down on her bed, Cream sitting on one side and Tails on the other. This was only their second meeting, taking place in Sonic's house they had to be quiet.  
"I-I don't think it is..." Tails trailed off, he was unsure himself as this 'awakening' was only a recent development. Upon hearing this Amy let out a sound with intended sexual implications, shortly followed by another punch in the arm from Cream.  
"Anyway, should we get to it then?" Amy grinned, standing up mid-sentence and practically dragging Tails into the closet. Upon entering the closet, Tails was surprised at the sheer amount of clothes Amy owned and gave out a little gasp.  
"You can pick anything you like! I think this'll look good on you!" Amy suggested, holding up a somewhat revealing maid dress.  
"Why do you even..." Tails gave the dress a look of disgust, before turning away quickly "Nevermind, I don't think that's a good fit for me."  
"Suit yourself!" Amy giggled, putting the dress down and backing out of the closet, "I'll give you some privacy."  
Tails ran his hand over many different clothes, dresses, skirts, shoulderless t-shirts, Amy had it all! Tails was thrilled, he had no idea what kind of outfit to go for. Though after several minutes of holding items up to himself and looking in the mirror, he had a rough idea of what suited him and what didn't. In the end, he'd decided to go with a lime green skirt and a chestnut mini jacket.  
Tails stepped out of the closet, one hand gripping his other arm and his head turned sideways, blushing slightly. There was complete silence, so Tails turned to them.  
"Well...? Don't leave me hanging guys." Tails couldn't look them directly in the eyes, despite the immense enjoyment he was feeling it was also incredibly stressful. Amy pulled a slightly angry face, though she soon realized this and tried to hide it.  
"You look better in those than I do..." Amy grumbled, turning away slightly.  
"What Amy's trying to say is you look amazing!" Cream exclaimed, standing up and holding Tails by the hands. Amy, now calmed down a little, turned back to Tails.  
"Do you mind if we take some pictures?" Amy asked, pulling a pink phone out of her pocket. Tails was unsure of what to say, usually, he'd say no but he'd had a sudden confidence boost.  
"O-okay!" Tails agreed softly, even managing to hold a tiny smile. Amy held up her phone and began to take a picture, but quickly put it down again.  
"You can't just stand there! Strike a pose or something!" Amy demanded, she was really getting into this.  
Tails looked terrified, but at this point, his enjoyment was outweighing the stress. He put both hands on his shoulders, tilted his body slightly and pushed one leg further forwards.  
"That's better!" Amy was overjoyed, and quickly took the photo, "Let's get some more!"  
Pose after pose, Tails and Amy were really enjoying themselves with Cream just staring, amazed at Amy's ability to get Tails out of his shell. They'd taken nine pictures at this point and were showing no sign of stopping, until Cream pointed out how late it was.  
"Let's get one more, yeah?" Amy asked, though it was a rhetorical question, he wasn't leaving without that tenth picture. Tails nodded in agreement. He bent his legs, put both his hands behind his head and tilting his head slightly, staring directly into the camera. Amy was about to take the picture but was quickly distracted by the opening of her bedroom door.  
"Amy, I-" Sonic walked in, holding a cup of coffee, though quickly stopped at the sight of Tails. Sonic couldn't continue speaking as his breath had been taken away entirely, he just stood there, making everyone panic.

"S-Sonic! I can e-explain!" Tails trembled, blushing and waving his hands around frantically in the air. Sonic had come down from the total panic state he was in, and let out a small sigh.  
"You don't have to explain anything, buddy. Whatever this is, I support you..." Sonic grinned and held up his thumb enthusiastically "...100 per cent!"  
Tails fell to his knees, the blush making his entire face a bright red. He looked back up at Sonic, who was standing in the doorway as nonchalantly as he could.  
"Thank you, Sonic." Tails stood back up and looked directly at Sonic, letting out a little giggle "I must look ridiculous!"  
"No, no! You look amazing!" Sonic walked closer to Tails and put his hand on Tails' shoulder before repeating "You look amazing" in a deeper, more meaningful tone. After a little silence, Sonic stood up and gravitated towards the door. He then turned back to the three of them.  
"I'd dress up with you if it'd make it easier!" Sonic said requested, though masked it with a jokey tone, Amy and Cream let out a little laugh but Tails' eyes lit up with joy. Sonic then turned back and walked out of the room.  
Sonic stood outside Amy's room and looked down at his now cold coffee, Tails had made him curious. 'Tails looked really cute in that outfit.' he thought, both in a sexual and slightly jealous way.

Suddenly the door swung open and Sonic was dragged back inside.  
"Tails! What are you doing!" Sonic asked, a slight loudness in his voice. Tails didn't respond, storming past Amy and Cream and going back into their closet. He closed the door behind him and let go of Sonic.  
"I've known you too long to know when something is or isn't a joke, Sonic" Tails, beaming with confidence, tilted his head sideways. Studying Sonics body figure, thinking of what'd look good on him. Sonic just stood there, trying to say something, anything, but he couldn't. Tails noticed something out of the corner of his eye and went to fetch it, he picked up a bright orange crop top and a pair of shorts before throwing them directly at Sonic.  
"Put these on," He commanded, before continuing to look for something. Then he found it, an orange pair of purely decorative glasses, and placed them on Sonics face. He stood back, taking in his masterpiece and smiled. Sonic finally opened his mouth to speak but was quickly silenced by Tails pushing him out of the closet, in more ways than one. Sonic was face to face with Amy, who was covering her mouth with her hands.  
"Sonic, I don't know what to say," Amy lowered her hands and stood up to get a better look "I have no words."  
"Is that a good thing?" Sonic said quietly, still in shock from everything that'd happened.  
"Of course it's a good thing!" Amy shouted, basically collapsing onto Sonic, though it was just a hug.  
After a little while, they'd all calmed down. Cream, yet again, pointed out the time, which reminded Amy of something.  
"Hey Tails, we never got that tenth picture because _someone_ interrupted us," Amy gestured to Sonic, before getting an idea "Hey! You two should pose together!"  
They were both a little hesitant at first but eventually, they both stood up and started thinking of a pose to do. They stood back to back, arms crossed and Tails staring into the camera. Sonic was looking away from the camera, blushing pretty hard. Not only was he in a more feminine outfit than he was used to, seeing Tails in clothes like that sparked something within him. He didn't know what it was, but it was certainly there.  
Finally, Amy took the picture.


End file.
